Southwinds Motel

This is a very tightly packed motel Style accommodation. I recommendation is you don't pull into the car park straight away because you might be in a different car park and trying to turn the car around is very tight without any parking spaces. We were in a little annex to the area which meant our car was in one car park but we walked slightly down the road to our room however it did mean that we had small swimming pool for around 10 rooms. It's an older property but it is being maintained well and it's a short walk to the far end of Duval Street. There is a shuttle bus service if you go out to the hotel turn right and walk to the bank there is a free bus that will take you around Key West. Interesting enough no one in the hotel seemed to know about it. Breakfast was good it's a grab and go situation but there was a good selection. Pool temperature was just right and although the hotel looks fairly full I actually had the whole pool to myself in the evening. There is a bar at the front which my adult children did use:-) if I was going to Key West again I would look at this hotel as a number one choice. The room is very large, the accommodation is in a quiet area but within easily walking distance of bars and restaurants.

Carlos and Peggy were great! Coffee was always on and included in the resort fee. Great for families and honeymooners. Singles not so good. The drive down was awful. It was a non-stop SPEED TRAP. Duval Street was only about 4 blocks away but I am elderly and it is hard for me to walk. I found no cabs when I needed them. When I finally got the energy and my pain pills kicked in, I walked to Duval Street with my cane and had a great time. The bartenders were all beautiful, friendly and they made me feel like it was 5 o'clock somewhere as soon as I ordered my first Margarita. It's actually a great walk for families, couples and crews but not for singles. The beach is awful. Duval's beach is better but nothing compared to Miami Dade, Broward and Palm Beach Counties. (any other Beach in Florida is better). There are a lot of watersports but I had no partner so It seemed risky to go solo on anything other than flotation devices so I used a couple noodles and floated near shore. The water was clean.

We stayed for 2 nights with our 2 kids. The room was comfortable, an had a kitchenette. There was a heated pool, bar with live music and a ice cream truck on property. We were able to walk to the southermost bouy, down Duval st, and Mallory square, which was helpful with limited parking in the city.

The room was tiled throughout and clean. It had a nice sink area and mini fridge. They provided a pack n play for our baby to sleep in. The room includes a parking space but sometimes the lot fills up and you have to park on the other side of the building down the block which is not ideal.

Our family of 4 stay was amazing from the start. We arrived earlier than expected and front desk staff was more than accommodating in that one of our rooms was all ready for us so they let us stash all our bags in that room while we explored Key West. The staff was friendly, helpful and courteous. This is not a fancy 5star “resort” but an upscale Motel. We were able to book tours and rent bikes at the front desk. Spent most days riding our bikes around and trying all the recommended places to eat (a must try are the Cracked Conch as they are better than the breaded conch fritters) and listening to all the live music. We spent most mornings lounging by the pool waiting for our adult kids to wake up or at the onsite outside bar. There is free laundry onsite which made traveling a lot lighter. Also a small grocery store across the street. They are located on a side street off of the quiet end of Duvall Street and walking distance to the southernmost point landmark. If we return to Key West this is hands down the place we will stay.

You cannot find a better value for your money in key west. Especially not this close to the southernmost point. location is great, felt safe. The room #7 was nice! large, a bedroom, a sitting room with pullout- the real bed was a “queen” but felt like king size. a kitchen with microwave and full size fridge. 2 pools with lots of seating, but they don’t get much sun in winter and aren’t heated so it was a bit too chilly, but not motel’s fault- most pools aren’t heated in Fla. staff was attentive, breakfast was included, yogurt, cereal, milk, muffins, juice, coffee. It saved us spending $100 for our family of 4 every day. Key West isn’t a cheap vacation but staying here helped us spend money on more important things, like excursions. AND we stayed over NYE with special treats waiting in the room! They had 4 professional 2024 cookies, beads, bottle of champagne, hats, a few other offerings to make our stay special. I was so impressed by those extra touches. Notable cons: cheap and damaged furniture/decor, but functional. Pool not heated. Tiny bathroom. And there is nowhere for them to store your luggage: check in is at 4, we got in at 1 and wanted to drop bags bc we knew room not ready. They allowed us to drop bags but they just sat there in the lobby unsecured until we got back. will absolutely stay here again when we travel with our kids. If we were just 2 adults, we would likely splurge on somewhere a little nicer.

I would recommend this to all my friends and family. Love the location and the hospitality for everyone of the staff. Great walking distance to everything.

Spacious room, very clean linens and comfortable bed. Air conditioning extremely cold, needed extra towels front desk sent staff member with warm laundered towels. Very quiet at night to sleep, the bar was great and the ice cream truck was a hit with our children. Walking distance to many great restaurants. Overall a great experience, will definitely stay here again.

We took a family vacay here from 7/6/23-7/8/23 and stayed in room 39. The staff is extraordinary!! Everyone is incredibly friendly and helpful. The rooms are of adequate size and clean. Our room had the bonus benefit of having a king and queen bed as opposed to two queens. Water pressure in Key West is crap overall so not really their fault, there was no hot water to speak of but in all honesty that worked for us…. Because the biggest issue I had was the antiquated window AC unit that basically didn’t work worth a crap. Let me tell you, July in Key West is swamp a$$ season and their is no recovering from that with out AC. The pools will stay a balmy 80+ degrees and the sun is hell bent on sizzling off your flesh and replacing it with cancer. Now, in all fairness, from my observations, they are updating rooms. Room 39 just hasn’t been addressed yet. So definitely worth a try, but only if you get a renovated room.

Duval Street with all it's hustle and bustle is right around the corner but far enough not to be a bother for a family. Unlike other places during our road trip, this motel kept its cleaning schedule daily, which is commendable, but not enough to justify the outrageous price they charge for a night during high season weekends. For almost $300 per night (with taxes and fees) we would have expected a decent breakfast but got a thin coffee, yoghurt and plastic-wrapped pastries instead. Better than nothing, but underwhelming considering the price. Again, this is a rather simple motel. You might be able to get a room for half of what we paid with two children. The motel is certainly family-friendly as others have noted.